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The Cool List: The Coolest Caribbean Hotels for 2020

caribbean cool hotels

El Blok in Vieques. (Photo by Elliott Anderson).

The Caribbean’s roster of high-design, forward-thinking, fun-loving hotels continues to grow. 

Everyone has a different definition of what’s cool — particularly when it comes to hotels. 

But a cool hotel should have an x-factor, a special quality that turns it into something more than just a collection of rooms — whether that’s from the way it looks, the way it sounds or the way it feels. 

Our eighth annual edition of the Cool List takes you on a journey across the Caribbean, with some hotels you may know and a host of hidden-away gems just begging to be discovered. 

Here is the 2020 edition of the CJ Cool List. 

The Fred, St Croix St Croix’s first new hotel in decades has injected major new energy into the heart of Frederiksted, and this playful, hip boutique continues to raise its game. The adults-only hotel has everything from a spa to a great stretch of beach to some of the most avant-garde decor you’ll see in the Caribbean Even better, it’s the perfect gateway to one of the buzziest destinations in the Caribbean, an island with a thriving culinary scene, beautiful beaches and a funky, forward-thinking vibe. It all adds up to our favorite “cool” hotel for 2020. 

caribbean hotels cool

Delfins Beach Resort, Bonaire The newest place to stay in Bonaire is a new level of hip for the Dutch Caribbean island. The beach bar is a food truck; it’s solar powered; the rooms are blissfully minimalist and, oh yeah, the restaurant is helmed by three-Michelin-star chefs from The Netherlands. 

Port Ferdinand, Barbados Residential resorts are one of the coolest things in travel, and this gorgeous boutique resort in Barbados has taken the concept to a new level. Capacious suites join amenities like an overwater pool, a superyacht marina, a golf simulator, a striking spa and the only Nikki Beach in the English-speaking Caribbean, all adding up to one of the coolest places to stay in the Caribbean right now. 

caribbean hotels cool

LTC Beach Hotel, Saint Martin At the center of a reborn Grand Case is this ultra-hip boutique hotel with just eight rooms, perched right on the beach. The on-site eatery is exquisite, there’s endless live music and the decor and service are the essence of French Caribbean chic. 

caribbean hotels cool

The Dunmore, Harbour Island, The Bahamas Harbour Island has long been one of the Caribbean’s capitals of cool, but The Dunmore, the classic beach resort set right on Pink Sand Beach, remains the height of Harbour hip. The rooms are a mix of barefoot chic and jet-set glamour, and the ambience marries playfulness with overwhelming serenity. 

caribbean hotels cool

La Suite Villa, Martinique You notice the dramatic art collection the moment you walk into this Trois Ilets-area hotel, where spacious rooms (some with plunge tubs) marry with an eclectic, carefree ambience and a signature eatery now helmed by a Michelin-star chef from Bordeaux. 

Eden Rock St Barths St Barth’s most iconic place to stay is back and better than ever, with its red roofs (and red-garbed staff) continuing to set the standard for an island where luxury and fashion are practically an Olympic sport. (And don’t forget there are villas here, too). 

OLV: Fifty Five, San Juan, Puerto Rico It’s hard to think of a sexier hotel anywhere in the Caribbean. The husband-and-wife team of Loisse Herger and Fernando Davila changed the game in San Juan’s Condado neighborhood with their first hotel, the O:live, and their newest offering is a sumptuous, indulgent, spectacularly designed boutique with a buzzing rooftop and what just might be the coolest showers in the Caribbean. 

caribbean hotels cool

Pearl Beach St Barth Long hidden away in plain sight in St Barth’s popular St Jean beach, the rebranded Pearl Beach (formerly Tom Beach) remains a tiny gem, with a boutique-sized pool that’s always hopping and one of the island’s best beach restaurants. 

South Point, Antigua We just love this hotel right on the water in Antigua’s English Harbour. It’s unique in the region: a residential resort aimed at independent-mind travelers that’s actually a boutique hotel, with ultra-sleek rooms (with kitchens), a beautiful little beach and pool and an always-energetic waterfront sushi and cocktail bar. 

Pagua Bay House, Dominica This tucked-away gem in Dominica has long been one of our favorites, with bright, beautiful “cabanas” and suites and a centerpiece outdoor deck that’s got out-of-this-world views (oh, and the locally-focused restaurant is a winner, too). 

caribbean hotels cool

The Island House, Nassau, The Bahamas Set at the edge of Nassau’s tony Lyford Cay neighborhood, this boutique has set a new standard for boutique hotel design in the wider region, with everything from a full-fledged cinema to squash courts to co-working spaces. There’s something for everyone here — a rather impressive proposition for a hotel with only 30 rooms. 

caribbean hotels cool

El Blok, Vieques, Puerto Rico Natanial Fuster’s dramatic boutique hotel has become Vieques’ signature place to stay, with 22 colorful, funky rooms, an impressive food and beverage program and a hot-tub-accented rooftop deck that’s a reason to visit all by itself. On an island that’s long been Puerto Rico’s beachy sanctuary, it’s a veritable town square.  

The Liming Bequia The Caribbean doesn’t get much cooler than Bequia, the lovable little jewel of the Grenadines, and the island’s newest hotel is a major addition. There are just nine villas and suites at The Liming (all with hot tubs or plunge pools), a boutique that manages to fuse Bequia’s laid-back tranquility with a dose of modern energy. 

caribbean hotels cool

Boardwalk Boutique Hotel, Aruba It was always Aruba’s best small hotel, and now the Palm Beach-area Boardwalk is officially a “boutique hotel.” The expanded property has only added more of its small-hotel charm, with delightfully designed casitas, a sparkling new poolscape and, happily, a new eco-friendly touch. (And yes, there’s even beach service on Palm Beach).


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